I think David Ramsey's points about living within your means and saving is good, but it doesn't apply to housing. 

If you are wanting to learn more about how to protect yourself as the PML, check out the book Lend to Live: Earn Hassle-Free Passive Income in Real Estate with Private Money Lending available in the BiggerPockets bookstore!

I live in a tenant friendly state hence the tenant normally wins under the circumstances unless you have evidence to back up your claim. 

You can either do an income based loan underwritten by your income and supported by financial documents or a DSCR loan if an investment property you don't live in. 

I am very eager to start taking action and learning but live in a high cost of living market (Boston) currently and for several reasons (need to save more, move to lower cost of living place etc.) will not be able to start for at least 1.5 years. 

You live there, so there's obviously something desirable about.

I have house hacked a bit, and have flipped 2 houses (homes I lived in).

My plan would be to live in it for a year and then start renting it out. 

I live in Winston Salem, NC.

The man currently living there is a retired wheelchair bound vet who always pays on time and so they have never felt right raising the rent as hes only living on his Army paycheck.House 3. rents for $800/m the loan will cost me $14,000 as a down payment and $6,000 closing costs, and should cash flow approx $225/m after mortgage payment are made.House 4.